Suitably protected mono- and di-saccharide residues associated with the glucuronic acid-containing repeat unit related to pentosan polysulfate have been prepared. The stereo-controlled coupling, using trichloroacetimidate chemistry, of certain of these is also described and the structure of a disaccharide so-formed has been confirmed by single-crystal X-ray analysis.
Supporting information for this article is available online at https://doi.org/10.1055/a-2126-0346. Included are an outline of the general synthetic protocols employed in this study, plots derived from the single-crystal X-ray analyses of compounds 17, 18 and 40 together with summaries of key NMR spectral data used to establish the structures of compounds 3, 12 and 13, 31 and 32 and 34.
Copies of the 1H and 13C NMR spectra of compounds 2, 3, 4 (R =Me), 5, 7, 9, 11–17, 19, 21–34 and 36–40 are also provided.
1c
Perez S,
Makshakova O,
Angulo J,
Bedini E,
Bisio A,
de Paz JL,
Fadda E,
Guerrini M,
Hricovini M,
Lisacek F,
Nieto PM,
Pagel K,
Paiardi G,
Richter R,
Samsonov SA,
Vivés RR,
Nikitovic D,
Blum SR.
JACS Au 2023; 3: 628
2Heparanase
. In
Advances in Experimental Medicine and Biology, Vol. 1221.
Vlodavsky I,
Sanderson R,
Ilan N.
Springer; Cham: 2020. https://doi.org/10.1007/978-3-030-34521-1_3
5f
de Boer C,
Armstrong Z,
Lit VA. J,
Brash U,
Ruijgrok G,
Boyango I,
Weitzenberg MM,
Schröder SP,
Sarris AJ. C,
Meeuwenoord NJ,
Bule P,
Kayal Y,
Iilan N,
Codée JD. C,
Vlodavsky I,
Overkleeft HS,
Davies GJ,
Wu L.
Proc. Natl. Acad. Sci. U.S.A. 2022; 119: e2203167119
5i
Doherty GG,
Ler GJ. M,
Wimmer N,
Bernhardt PV,
Ashmus RA,
Vocadlo DJ,
Armstrong Z,
Davies GJ,
Maccarana M,
Li J.-p,
Kayal Y,
Ferro V.
ChemBioChem 2023; 24: e202200619
5j
Yang C,
Deng Y,
Wang Y,
Xia C,
Mehta AY,
Baker KJ,
Samal A,
Booneimsri P,
Lertmaneedang C,
Hwang S,
Flynn JP,
Cao M,
Liu C,
Zhu AC,
Cummings RD,
Lin C,
Mohanty U,
Niu J.
Chem. Sci. 2023; 14: 3514
10 Recently we have shown that the exhaustive sulfation of compounds related to 1 results in the associated xylose residues preferentially adopting a 1C4 conformation: Vo Y., Schwartz B. D., Onagi H., Ward J. S., Gardiner M. G., Banwell M. G., Nelms K., Malins L. R.; Chem. Eur. J.; 2021, 27: 9830; However, for the sake of consistency with the prior literature concerned with such compounds, in this paper we show such residues in the 4C1 conformation.
11a
Freeman C,
Liu L,
Banwell MG,
Brown KJ,
Bezos A,
Ferro V,
Parish CR.
J. Biol. Chem. 2005; 280: 8842
12 The realization of related objectives has recently been reported by Madsen et al., see:
Underlin EN,
d’Errico C,
Böhm M,
Madsen R.
Eur. J. Org. Chem. 2020; 3050
